Notes

Task management software for digital projects

En route to Drupal BADCamp, which IMHO was a very good camp, I read about a project management session describing an agency’s journey from one task management product to another. Reflecting on my checkered past in that area, I came up with a list of such products I’ve used over the past 16 years:

Bugzilla, 2000 – 2002

A custom CFM App, 2003-2004

Gootodo, 2004-2007

Tenrox, 2004-200

Excel, 2005-2008

Remember the Milk, 2007-2010

Salesforce CRM, 2007-2008

Basecamp Classic, 2008-2010

Open Atrium, 2009-2011

Tada List, 2009

Workflowy, 2010-2016

Google Tasks, 2010

Fogbugz, 2011-2013

Smart Sheetz, 2013

Teamwork PM, 2013-2015

Google Office/Sheets, 2011-2016

InVision, 2014-2015

Basecamp 2, 2012-2016

Wrike, 2014-2015

JIRA, 2015-2016

Evernote, 2016

Trello, 2016

Note: the items in blue make up the courageous history of task management products for just one firm over an 8 year period

General Observations

Task management is one feature that people will use no matter what software product it’s tacked it on to

For some of these products, task management is core functionality but is not a strength. For example, Basecamp 2 is not so good at task management but pretty good at moving group conversation out of email

A task/project management product that also does billing and invoicing is a rare species, though Tenrox, which is enterprise-grade software, is supposedly able to, as is JIRA and Tempo.

There are some product features we are loath to use, such as the notes field when entering hours; task management is one feature that people will use no matter what software product it’s tacked on to.

JIRA seems like the most scalable and flexible product. However, it needs a very empathic spirit guide/product implementation expert to make it usable to a broad number of people.

Of course, I’ve never used Harvest beyond a pretend-work demo, so perhaps I haven’t tried the best products out there. But no matter what the tool is, it will only work well with smart usage principles.

My observations on usage

Commenting. There is a fine line between too little and too much commentary when creating or updating a task. Too little sometimes means you haven’t spent enough time considering the work at hand; too much usually means the same thing. Just right is when you take a moment to think things through and leave just enough information to help the next person act without asking follow-up questions for clarification (“so.. what is this thing about”?).

Ideally, you can nail “the ask” in the subject line of a task item, then use the body area to copy and paste useful information, like links, screenshots, or the relevant communications from a client email. Here are examples of task item subject lines that say too little, too much, and just the right amount, in that order:

Scope. As with commenting on a task, there is an art to apportioning just the right amount of work to one. But just because a task’s commentary should be succinct doesn’t mean the task should be small in scope. In fact, the rule of thumb is to create as few tasks as possible, in general. That keeps us away from the other edge of the spectrum, infinite tasks because task creep happens, and that will lead to a confusing interface for everybody.

When a worker looks at a project or a task list or filters their tasks using a product like JIRA, it’s confusing to have more than about 10 tasks to take in at once. If you’re worried about a task’s scope getting too big when you are creating or editing a task, just ask the task’s assignee, as in: “This task is getting pretty big — do you want this broken up into separate tasks?”.

One person per task. What’s funny is that we invest all this capital and ingenuity in building task management software and then people use it to assign a single task to multiple people. That never works; in fact, you could argue that the point of task management software is to break down projects into pieces of work that individuals can do by themselves. Just because your task management tool (email is a great example) may allow you to ask many people to do the same thing, doesn’t mean you should use it that way.

There are some edge cases where multiple do need to do the exact same thing, like update their contact information, but for most project work, one person per task max is the rule to live by.

My observation is that whenever one person is found adequate to the discharge of a duty… it is worse executed by two persons, and scarcely done at all if three or more are employed therein.

~ George Washington

Centralization into one tool. We’re increasingly working in partnerships in the digital space. Boutique firms need to team up to deliver enterprise work that they otherwise wouldn’t have the capacity or breadth of expertise to deliver on. But multiple teams mean lots of tools, of all kinds; one firm uses Basecamp 2, another Teamwork PM. Another uses a Google sheet. At the same time, products like Google Sheets and InVision aren’t even meant for task management but they sure allow the creation and assignment of work, multiplying the total number task management products in play.

So each team should have their task management “product of record”. You may not be able to prevent multiple task management products from being used on the same project, but at least you can have a “one tool to rule them all” rule.

Migrating. It’s not so bad, once you get some practice, to migrate from one product to another. The key is to use a product of record approach, then make a certain transition only once the new tool is thoroughly tested. I would encourage digital agencies and teams to experiment widely with task management tools and find the one that’s right for you.

And that goes for all kinds of business tools: document storage, team chat, conference call software, hours tracking, invoicing, CRM, etc. Every agency will have a slightly different and constantly shifting spectrum of software they use to do business; task management has to find a way to fit in. So don’t be afraid to migrate tools from time to time.

Billing. It’s wise to correlate billing and task management in a systematic way. And that makes it all the more important to corral disparately created tasks into the “product of record” so hours are accurately billed. What’s wonderful about JIRA and Tempo together is that task tracking and commenting integrate with hours tracking, a better UX for anyone who needs to communicate the work they have done, and for anyone who needs to find a way to get the company paid for doing that work.